Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

Indigo is the blue dye used in jeans. It was first obtained from plants of the indigoftera type, but nowadays it is made almost completely by synthetic methods. Indigo does not dissolve in water, although this drawback can be overcome by converting it into the colourless, water-soluble leuco-indigo.
(a(i))[1]

Give the molecular formula for indigo.

(a(ii))[2]

Name three functional groups present in indigo.

(b(i))[1]

What type of reaction does the conversion of indigo into leuco-indigo involve?

(b(ii))[1]

Suggest a laboratory reagent to use in this reaction.

(c)[5]

Suggest two chemical tests that could distinguish indigo from leuco-indigo. Present your answers in the table below.

(d(i))[2]

When indigo is heated with hydrogen and a nickel catalyst, compound $A$, $\text{C}_{16}\text{H}_{28}\text{N}_2\text{O}_2$, is produced. Suggest a structure for $A$.

(d(ii))[1]

Calculate the volume of hydrogen, at room temperature and pressure, that would be absorbed if $2.50\ \text{g}$ of indigo reacted in this way. volume $= \ldots\ldots\ldots\ldots\ldots\ldots\ldots\ \text{dm}^3$

(e)[3]

Suggest the structure of the product formed when indigo reacts with excess $\text{Br}_2\text{(aq)}$.

Worked solution & mark scheme

This 16-mark question has a full step-by-step worked solution and mark scheme. One marking point: $\mathrm{C_{16}H_{10}N_2O_2}$

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